I found myself belly-up, floating on the Caribbean Sea, and feeling extremely privileged to be enjoying the perks of working in a distributed company such as Automattic.

Getting together on a regular basis is one of the key ingredients that allows us to work effectively on a distributed company. At Automattic, teams meet two to three times a year for about a week each time to work together on a project, have some in-person discussions, and more importantly, to bond. We call these gatherings meetups.

We have a budget and we can choose, within reason, any place on earth to get together. It’s one of my favorite perks in this company.

Organizing these events can be quite overwhelming. There are a lot of things to take into account. This ranges from finding a location that won’t require a cumbersome visa application process, to choosing restaurants with options that accommodate everyone’s preferences. Despite that, I really enjoy all the logistics planning.

One great advantage that we have at Automattic is that we document all of those meetups on our internal blog tool. So, it’s easy to check which cities are the most popular, costs, and the overall experience of other teams. It can save a lot of research time. I’m guilty of copy-pasting almost the entire logistics of another team’s meetup; hotel, restaurants, co-working space, social activities, etc.

Here are a few tips that have been useful to me.

Location, location, location

Finding the right location is the most crucial aspect of a successful meetup. The number one goal for these events, at least for me, is the social bonding, the collective memories created together. And in that regard, the scenery matters a lot. It’s not the same to have a discussion with a beautiful view in the background than to have that same discussion from a hotel near the airport. The bonding of those synapses will be much stronger with a view like this:

To simplify the selection process, my recommendation is to come up with a short list of destinations to chose from. That works best if you know your team really well. Otherwise, it’s better to ask for suggestions within some specific constraints:

• Easy of access. Direct flights are preferable. Although if the place is amazing, it might be worth the hassle.
• Season. Don’t go to Las Vegas in the summer, or to the Caribbean during rain season.
• Visa requirements. Try to avoid making anyone go to a cumbersome visa application and risk not being able to come.
• Specific region of the planet. It’s easier to suggest a destination when there are fewer options to choose from–e.g., Central America, Southern Europe, East Coast USA.

Delegation

Even if you enjoy the organizational aspect of meetups, doing it all by yourself can be too much. This is especially true if you’re a big group. My recommendation is to delegate three main areas to different people:

• Lodging. Step one is finding out the group preference. A big house or hotel rooms. Some people prefer private hotel rooms. In that case, you’ll also need to find an additional place to work. This could be a co-working space or a hotel meeting room. I usually prefer big houses–you have more time for social iterations and casual discussions. The challenge is finding a house big enough with private rooms and toilets. Another possibility that works well is combining a big house with nearby hotels.
• Food. The person in charge of food should find out the group dietary restrictions. They should make sure to pick restaurants that can accommodate everyone’s dietary restrictions and preferences. It is important to make reservations for most days. Trying to improvise on the spot every day can be very stressful for the person in charge.
• Social activities. If you have budget for social activities like excursions, tour guides, museums, etc., it’s also important to plan that in advance. Ask someone to do a little research and come with some options so the group can vote.

Agenda planning

Different people expect different use of their time during team meetups. Some prefer more hands on work and coming back with something concrete–a prototype, kickstarting a project, squashing bugs together, etc. Some prefer to spend their time discussing topics in person–roadmap or project planning, team retrospectives, technical discussions, etc. Even if you try to balance those two things, it’s impossible to make everyone happy. The best you can do is to clarify things upfront.

My recommendation is to alternate and experiment in this spectrum. If you’re close to end of the end year, it might make sense to focus roadmap planning. If you have big initiative coming up, it might be a good idea to kickstart projects in person. No matter the option, try to get everyone involved in the agenda creation. What has worked well for me was asking people to volunteer for flash talks or short presentations on anything related or unrelated to the work we do.

Lastly, but just as important, be sure to schedule time for ice-breakers, social activities, and plenty of breaks to rest. Without careful planning, team meetups can become very intense, especially if you underestimate the need for rest. I like to keep the agenda flexible and adjusting when needed. Read the room, be explicit, ask about their energy levels.

Conclusion

The truth is, I don’t know of any other company doing team meetups like we do it at Automattic. So I understand my tips aren’t as useful for anyone outside the company. However, maybe they can be used to convince someone in charge to experiment with this format. Or maybe this post can convince you to apply for a job at Automattic.